Sixteen Days, Two Neighborhoods: Highland Park's Fall Festival Split

Park on Central Avenue for one of these festivals and you will walk right into the next one. Park in the same spot for the one in between and you will be nowhere near it. That is the quiet complication buried in Highland Park's fall calendar this year: three flagship events land within sixteen days of each other, but they no longer share a footprint the way they used to.

The city's Scarecrow Trail closes out the summer concert series on September 25 at Port Clinton Square, downtown. The next night, September 26, Oktoberfest fires up along Dean Avenue and inside Jens Jensen Park, in the Ravinia District, east across Green Bay Road from downtown. Then on October 10, the calendar swings back downtown for Stews & Brews, now in its fifth year at Port Clinton Square and Central Avenue. Same six weeks, same city, two distinct neighborhoods doing the hosting.

If you have lived here through a few autumns, you already sense that Highland Park treats downtown and Ravinia as different rooms in the same house. What is new this year is how deliberately the fall calendar uses both rooms back to back, and it changes how you should think about parking, transit, and which Friday or Saturday actually works for your family.

The Sixteen Days, In Order

Here is what is actually on the books, and where:

Scarecrow Trail is the city's third year running the event under that name, closing out the Downtown Concerts at Port Clinton Square series. More than two dozen decorated scarecrows will be spread through the Central Business District, alongside face painting, airbrush tattoos, pumpkin crafts, and a run of Wizard of Oz characters. Attendees vote for Best in Show Scarecrow, and the whole footprint stays where the summer concerts have been all season, which means anyone who has found downtown parking for a Friday night show already knows the drill for this one.

Oktoberfest is where the map actually changes. This year's event uses Dean Avenue in addition to Jens Jensen Park, at 540 Roger Williams Avenue, a footprint expansion the city has flagged directly on its own event page. Dean Avenue is the same stretch that hosts Food Truck Thursdays all summer, closed to cars between Roger Williams and St. Johns avenues, so the city is essentially borrowing its warm-weather layout and running Oktoberfest through it in the fall. Expect the returning stein-holding contest, hammerschlagen, axe throwing, and a headlining band, all inside the Ravinia District rather than downtown.

Stews & Brews returns to the more familiar downtown footprint, spread across Port Clinton Square and Central Avenue for a fifth year. The city has said this edition adds more fire pits and heat towers along with a dedicated children's programming window from 4 to 6 p.m., which matters if you are timing a visit around nap schedules or an early dinner.

Why the Beer Garden Crossed Green Bay Road

Ravinia's status as its own district is not a marketing conceit. The neighborhood was an independent village before Highland Park annexed it in 1899, and it kept its own commercial spine along Roger Williams Avenue, separate enough from downtown that the city still treats it as a distinct business district today. That separation is exactly why Oktoberfest landing there this year is worth noticing rather than shrugging off. It is not a downtown event that happens to have moved streets. It is a fall festival built inside a neighborhood that spends its summer running a completely different kind of programming, the Ravinia Farmers Market chief among them, now entering its 48th season and running Wednesdays through October 28.

Steep Ravine Brewing Company threads through both ends of the fall calendar in a way that is easy to miss unless you are looking for it. The brewery has been the production partner behind past Oktoberfest events in Ravinia, and it also shows up on the roster of restaurants that have poured for Stews & Brews downtown. One business, two neighborhoods, two different fall weekends. If you are trying to understand how tightly Highland Park's food and beverage scene is stitched across its business districts, that is as clean an example as you will find.

Getting to Each One Without Guessing

Because Oktoberfest sits outside downtown, the city's own logistics guidance for it looks different from what you would use for Stews & Brews or the Scarecrow Trail. For Ravinia, the suggested routes are the Green Bay Trail, which connects to the Robert McClory Bike Trail, or Metra service to the Ravinia Station on Roger Williams Avenue. Driving in means Lake Shore Drive to Sheridan Road or U.S. 41, exiting at Clavey Road east to Green Bay Road, then east on Roger Williams. Free parking is available, but it is Ravinia District parking, not the downtown lots most residents default to.

Downtown events keep the logic simpler. Port Clinton Square sits at 600 Central Avenue, walkable from most of the Central Business District, and it is the same square residents already use for the Port Clinton Art Festival earlier in the season.

The practical takeaway is not complicated, but it is easy to get wrong if you are running on autopilot from last year: do not assume the Oktoberfest exit you took off U.S. 41 in past seasons still gets you closest to this year's event. The neighborhood changed, so the approach should too.

What's Actually on the Table at Stews & Brews

Stews & Brews has built its identity around not being a standard chili cook-off. In its fourth year, the lineup of participating restaurants included BWB Shakes, Cafe Dacha, Central Café, DeNucci's, Judy's Pizza, Lynfred Winery, Michael's Grill & Salad Bar, Ordo, Steep Ravine Brewing Company, Tamales, and Yana's Speakeasy, serving everything from Hungarian goulash to lamb stew to pozole alongside mulled cider, spiced wine, and craft beer. The event has consistently closed with a People's Choice vote for favorite stew and favorite brew, decided by QR code voting on site. Whether every one of those specific restaurants returns for the fifth year, the format and the roster of Highland Park kitchens behind it are well established at this point, which is part of why the event has grown its footprint and its hours each season.

The Overlap That Matters for Families

Look closely at the hours and a scheduling detail shows up that is easy to miss on a first read of the calendar. Scarecrow Trail and Oktoberfest both run 4 to 8 p.m. on consecutive nights, and both lean into family programming during that window, face painting and pumpkin crafts downtown, family-friendly games and dancing in Ravinia. If you are trying to do both with kids in tow, you are looking at two separate early-evening outings on back-to-back days rather than one relaxed weekend of drop-in visits. Stews & Brews, with its dedicated 4 to 6 p.m. children's block, is easier to treat as a single stop before the evening shifts toward the adult crowd and the fire pits.

None of this is a complaint about the calendar. It is simply what it takes to actually use it well this year, now that downtown and Ravinia are each carrying real weight in the same six weeks instead of one district hosting nearly everything.

The Point

Highland Park's fall used to read as one long downtown season with a farmers market on the side in Ravinia. This year's calendar treats the two neighborhoods as equal partners for the first time in recent memory, Oktoberfest anchoring Ravinia's fall while downtown keeps its Scarecrow Trail and Stews & Brews traditions intact. If you have spent years assuming every fall festival funnels back to Central Avenue, this is the season to recheck that assumption before you circle a date on the calendar.

Whether you are planning your own weekend around these events or simply noticing how Highland Park's neighborhoods keep evolving in relation to each other, that kind of local texture is exactly what we track at The GGL Group. If you are curious what else is shifting in Highland Park or any of the North Shore communities we call home, reach out and Schedule A Call.